EP3233033A1 - Resorcinol derivatives in compositions for simultaneous reshaping and colouring of keratinous fibres - Google Patents
Resorcinol derivatives in compositions for simultaneous reshaping and colouring of keratinous fibresInfo
- Publication number
- EP3233033A1 EP3233033A1 EP15801358.1A EP15801358A EP3233033A1 EP 3233033 A1 EP3233033 A1 EP 3233033A1 EP 15801358 A EP15801358 A EP 15801358A EP 3233033 A1 EP3233033 A1 EP 3233033A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- preparation
- hair
- acid
- kit
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title claims abstract description 39
- 238000004040 coloring Methods 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 title description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 162
- 239000000975 dye Substances 0.000 claims abstract description 88
- 210000004209 hair Anatomy 0.000 claims abstract description 87
- 230000003647 oxidation Effects 0.000 claims abstract description 61
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 61
- 239000002243 precursor Substances 0.000 claims abstract description 52
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 51
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 31
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims abstract description 19
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims abstract description 12
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 claims abstract description 10
- LHGQFZQWSOXLEW-UHFFFAOYSA-N 1h-pyrazole-4,5-diamine Chemical class NC=1C=NNC=1N LHGQFZQWSOXLEW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000004989 p-phenylenediamines Chemical class 0.000 claims abstract description 8
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical class NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 58
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- 238000000034 method Methods 0.000 claims description 42
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- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000004043 dyeing Methods 0.000 claims description 34
- 238000004806 packaging method and process Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 238000009499 grossing Methods 0.000 claims description 28
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- 239000003086 colorant Substances 0.000 claims description 14
- 230000001590 oxidative effect Effects 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- 230000008961 swelling Effects 0.000 claims description 10
- 238000010186 staining Methods 0.000 claims description 9
- AVKBLCWBDLLVRL-UHFFFAOYSA-N 2-(methoxymethyl)benzene-1,4-diamine Chemical compound COCC1=CC(N)=CC=C1N AVKBLCWBDLLVRL-UHFFFAOYSA-N 0.000 claims description 8
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003581 cosmetic carrier Substances 0.000 claims description 8
- 235000018417 cysteine Nutrition 0.000 claims description 8
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 8
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 7
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 7
- 235000010356 sorbitol Nutrition 0.000 claims description 7
- 229960002920 sorbitol Drugs 0.000 claims description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 6
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- KDBUTNSQYYLYOY-UHFFFAOYSA-N 2-(4,5-diaminopyrazol-1-yl)ethanol Chemical compound NC=1C=NN(CCO)C=1N KDBUTNSQYYLYOY-UHFFFAOYSA-N 0.000 claims description 5
- RBUQOUQQUQCSAU-UHFFFAOYSA-N 2-(4-aminoanilino)ethanol Chemical compound NC1=CC=C(NCCO)C=C1 RBUQOUQQUQCSAU-UHFFFAOYSA-N 0.000 claims description 5
- 238000007493 shaping process Methods 0.000 claims description 5
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- ISBRQFNLCJBQKZ-UHFFFAOYSA-N 2-oxopyrrolidine-1-carboxylic acid;5-oxopyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCC(=O)N1.OC(=O)N1CCCC1=O ISBRQFNLCJBQKZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000118 hair dye Substances 0.000 claims description 3
- NJTGANWAUPEOAX-UHFFFAOYSA-N molport-023-220-454 Chemical compound OCC(O)CO.OCC(O)CO NJTGANWAUPEOAX-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 abstract description 7
- 238000012856 packing Methods 0.000 abstract 1
- 102000011782 Keratins Human genes 0.000 description 27
- 108010076876 Keratins Proteins 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 22
- 239000007800 oxidant agent Substances 0.000 description 19
- 239000003638 chemical reducing agent Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- 230000009466 transformation Effects 0.000 description 15
- 230000008569 process Effects 0.000 description 13
- 229960001755 resorcinol Drugs 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 150000003840 hydrochlorides Chemical class 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 230000003113 alkalizing effect Effects 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 235000013877 carbamide Nutrition 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 239000000982 direct dye Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000003700 hair damage Effects 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000002280 amphoteric surfactant Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- VRDAELYOGRCZQD-NFLRKZIHSA-M sodium;4-[(2z)-2-[(5e)-5-[(2,4-dimethylphenyl)hydrazinylidene]-4,6-dioxocyclohex-2-en-1-ylidene]hydrazinyl]benzenesulfonate Chemical compound [Na+].CC1=CC(C)=CC=C1N\N=C(/C(=O)C=C\1)C(=O)C/1=N\NC1=CC=C(S([O-])(=O)=O)C=C1 VRDAELYOGRCZQD-NFLRKZIHSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 235000012756 tartrazine Nutrition 0.000 description 5
- 239000004149 tartrazine Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002888 zwitterionic surfactant Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- 239000004475 Arginine Substances 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 150000004665 fatty acids Chemical class 0.000 description 4
- WDPIZEKLJKBSOZ-UHFFFAOYSA-M green s Chemical compound [Na+].C1=CC(N(C)C)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1O)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](C)C)C=C1 WDPIZEKLJKBSOZ-UHFFFAOYSA-M 0.000 description 4
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 4
- 238000005691 oxidative coupling reaction Methods 0.000 description 4
- 235000012752 quinoline yellow Nutrition 0.000 description 4
- 238000007634 remodeling Methods 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
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- KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 description 3
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 3
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- 235000012735 amaranth Nutrition 0.000 description 3
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- FPAYXBWMYIMERV-UHFFFAOYSA-L disodium;5-methyl-2-[[4-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=CC=C(C)C=C1S([O-])(=O)=O FPAYXBWMYIMERV-UHFFFAOYSA-L 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
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- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 3
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- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- ZGZHWIAQICBGKN-UHFFFAOYSA-N 1-nonanoylpyrrolidine-2,5-dione Chemical compound CCCCCCCCC(=O)N1C(=O)CCC1=O ZGZHWIAQICBGKN-UHFFFAOYSA-N 0.000 description 2
- XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 2
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- OWWAUBQOFLVUMS-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-ol Chemical compound OC1=CC=CC2=C1CCN2 OWWAUBQOFLVUMS-UHFFFAOYSA-N 0.000 description 2
- JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 description 2
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- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 description 1
- 229940081510 piroctone olamine Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004175 ponceau 4R Substances 0.000 description 1
- 235000012731 ponceau 4R Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 description 1
- AYQGOOLZDOHXAY-UHFFFAOYSA-M sodium;3-[[4-[(2-chlorophenyl)-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(\C(=C\2C(=CC(C=C/2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC=CC=2)Cl)C(C)=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AYQGOOLZDOHXAY-UHFFFAOYSA-M 0.000 description 1
- SHBDDIJUSNNBLQ-UHFFFAOYSA-M sodium;3-[[4-[(2-chlorophenyl)-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)Cl)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SHBDDIJUSNNBLQ-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-N 0.000 description 1
- FTUYQIPAPWPHNC-UHFFFAOYSA-M sodium;4-[[4-[benzyl(ethyl)amino]phenyl]-[4-[benzyl(ethyl)azaniumylidene]cyclohexa-2,5-dien-1-ylidene]methyl]benzene-1,3-disulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=CC=CC=2)C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC=C1 FTUYQIPAPWPHNC-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- DWKARHJHPSUOBW-UHFFFAOYSA-N trimethyl-[3-[(2e)-2-(3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)hydrazinyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(O)=C1N=NC1=CC=CC([N+](C)(C)C)=C1 DWKARHJHPSUOBW-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/22—Peroxides; Oxygen; Ozone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
- A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/87—Application Devices; Containers; Packaging
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/88—Two- or multipart kits
- A61K2800/882—Mixing prior to application
Definitions
- the present invention is in the field of cosmetics and relates to multi-component packaging units for the simultaneous remodeling and dyeing of keratinic fibers, in particular human hair, which comprise at least two separately prepared preparations (A) and (B).
- the first preparation (A) contains one or more resorcinol derivatives and developer-type oxidation dye precursors and is characterized by a molar excess of resorcinol derivatives.
- the second preparation (B) contains hydrogen peroxide.
- a second object of the present invention is a process for the simultaneous shaping and dyeing of keratinic fibers, in which the preparations of the aforementioned multicomponent packaging unit are used.
- a third object of the present invention is the use of resorcinol and its derivatives in oxidative dyes for reshaping human hair.
- the user uses cosmetic forming agents.
- a permanent transformation of keratinous fibers is usually carried out in such a way that the fiber is mechanically deformed and the deformation is determined by suitable aids.
- the fiber Before, during or after this deformation, the fiber is treated with a keratin reducing preparation. After a rinsing operation, the fiber is then treated with an oxidizing agent preparation in the so-called fixing step, rinsed and freed from the forming aids (e.g., winders, papillots) after or during the fusing step.
- the keratin reducing component is a mercaptan, e.g.
- Ammonium thioglycolate is used, this part of the disulfide bridges of the keratin molecule cleaves to -SH groups, so that there is a softening of keratin fibers.
- disulfide bridges are knotted in the hair keratin, so that the Keratinge Shege is fixed in the predetermined deformation.
- sulfite instead of the mercaptans for hair styling.
- the frizzy hair is either on winder with a large diameter of usually more wound as 15 mm or the hair combed smooth under the action of the keratin reducing composition.
- the fiber is also possible to smooth the fiber on a smoothing board or to smooth the hair during the smoothing process with a comb.
- Smoothing boards are usually rectangular boards, eg made of plastic.
- the fiber is wetted with the keratin reducing preparation.
- alkaline reshaping agents in contrast to reshaping with keratin reducing and oxidizing compositions, do not result in reshaping of the disulfide bridges, but in destruction of the disulfide bridges to form monosulfide bridges.
- the pH of the alkaline reforming agent is usually in the range of 11-14, preferably 12-13.
- oxidation colorants To achieve permanent, intense colorations with good fastness properties so-called oxidation colorants are used. Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components. The developer components form the actual dyes under the influence of oxidants coupled with one or more coupler components. The oxidation colorants are characterized by intensive, outstanding, long-lasting dyeing results.
- EP 352 375 A1, EP 1 287 812 A2 and DE 10 2005 061 023 A1 disclose processes for the simultaneous shaping and dyeing of hair, in which a keratin-reducing preparation is used which already contains the necessary dyes and / or dye precursors. All of these methods known in the art are based on the use of a reducing agent and subsequent fixation by an oxidizing agent, wherein dyes (or dye precursors) are added either to the reducing agent component or to the subsequent oxidizing agent component employed.
- disulfide cystine units are first reductively cleaved to cysteine, but can not be fully restored in the subsequent fixation, since a part of the cysteine converts into side reactions to cysteine or cysteic acid.
- the transferred in the deformation in the plastic state hair so hardened though by the oxidative fixation, but does not revert to the original chemical or physical state.
- a curly-or alternatively-smoothed-hair which is internally stressed, thermodynamically is not in the most stable state, contains new amino acids (such as cysteine oxides and cysteic acid) and is incompletely cross-linked.
- the user takes this condition as a more or less pronounced hair damage was that - as the use of reducing agents process-related can not be avoided - a general drawback of all these transformation processes.
- a process for the simultaneous transformation and dyeing of keratin fibers which does not have these disadvantages, is not known from the prior art.
- a further object of the present invention was therefore to find means for the simultaneous transformation and coloring of keratinic fibers, in particular human hair, which allow both the transformation and the coloring, but without the two methods adversely affecting each other, and without an unpredictable deformation and staining result would occur by these mutual influence.
- the resorcinol derivatives present in excess are responsible both for a smoothing of the hair and - together with the other oxidation dye precursors and the oxidizing agent - for a coloring of the hair. In this way it was possible to permanently reshape and dye the hair at the same time. An unpredictable shift in shade of the color result or an unpredictable weakening of the deformation result was not observed in this context.
- the ready-to-use agent containing the oxidizing agent, developing type oxidation dyes and, in addition, molar excess of certain resorcinol derivatives is provided in the form of a multi-component kit of at least two separately prepared formulations (A) and (B), wherein the oxidation dye precursors and resorcinols are contained in the preparation (A) and the preparation (B) contains the oxidizing agent (hydrogen peroxide).
- a first subject of the present invention is a multi-component packaging unit (kit-of-parts) for reshaping and dyeing keratinic fibers, in particular human hair, comprising at least two separately prepared preparations (A) and (B), wherein
- (A1) one or more resorcinol derivatives from the group of resorcinol, 2-methylresorcinol and 4-chlororesorcinol, and
- (A2) one or more oxidation dye precursors from the group of p-phenylenediamines, the p-aminophenols, the 2,4,5,6-tetraamiopyrimidines, the 4,5-diamino pyrazoles, and / or their physiologically acceptable salts , and
- (B1) contains hydrogen peroxide
- transformation of keratinic fibers is understood to mean a permanent deformation which comprises a wave or crimping of the keratin fibers or may also be a smoothing of the keratin fibers.
- Permanent transformations are transformations that are still present or visible after at least one hair wash.
- dyeing agent for keratinic fibers refers to oxidative dyeing agents
- the formation of the dyeing takes place by reaction of the oxidation dye precursors of the developer type (A2) with the resorcinol derivatives acting as couplers under the influence of the oxidizing agent hydrogen peroxide
- the keratin fiber is simultaneously more or less lightened during dyeing since the oxidizing agent not only enhances the dye formation process of the dye Developers and couplers initiated, but also the hair-borne pigments (melanins) oxidatively destroyed.
- Keratin fibers are wool, furs, feathers and especially human hair.
- the colorants of the invention can in principle but also for dyeing other natural fibers such.
- cotton, jute, sisal, linen or silk modified natural fibers, such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose can be used.
- the preparations (A) and (B) contain all the essential components in each case in a cosmetic carrier.
- the cosmetic carrier can be a suitable aqueous or aqueous-alcoholic carrier.
- the agent in the form of a cream, an emulsion, a gel or in the form of a surfactant-containing foaming solution, such as a shampoo, a Schaumaerosols, a foam formulation or in the form of another preparation which is suitable for use on the hair be applied to the keratinic fibers.
- the multicomponent packaging unit (kit-of-parts) comprises at least two separately prepared preparations, a first preparation (A) and a second preparation (B).
- the preparation (A) contains in this case in a cosmetic carrier
- resorcinol derivatives from the group consisting of resorcinol, 2-methylresorcinol and 4-chlororesorcinol, and
- A2 one or more oxidation dye precursors from the group of p-phenylenediamines, p-aminophenols, 2,4,5,6-tetraamiopyrimidines and 4,5-diaminopyrazoles.
- the resorcinol derivatives (A1) are resorcinol, 2-methylresorcinol and / or 4-chlororesorcinol. A simultaneous smoothing and coloring effect could be observed when using all three resorcinol derivatives.
- Resorcinol is the compound of formula (I)
- 2-methylresorcinol is the compound of formula (II)
- 4-chlororesorcinol is the compound of formula (III).
- the resorcinol derivatives (A1) are preferably used in specific quantitative ranges.
- the first preparation (A) one or more resorcinol derivatives (A1) from the group of resorcinol, 2-methylresorcinol and 4-chlororesorcinol in a total amount of 1, 0 to 15.0% by weight, preferably from From 2.0 to 13.0% by weight, more preferably from 3.0 to 12.0% by weight, even more preferably from 4.0 to 1 1, 0% by weight and very particularly preferably from 5, 0 to 10.5 wt .-% contains.
- Calculation basis for these quantities in wt .-% here is the total weight of all Resorcinderivate from group (A1), which is set to the total weight of the preparation (A) in relation.
- a multi-component packaging unit (kit-of-parts) according to the invention is characterized in that the first preparation (A), based on the total weight of the preparation (A),
- (A1) one or more resorcinol derivatives from the group of resorcinol, 2-methylresorcinol and 4-chlororesorcinol in a total amount of 1, 0 to 15.0% by weight, preferably 2.0 to 13.0% by weight preferably from 3.0 to 12.0 wt .-%, even more preferably from 4.0 to 1 1, 0 wt .-% and most preferably from 5.0 to 10.5 wt .-%.
- the oxidation dye precursors (A2) furthermore contained in the preparation (A) are compounds from the group of p-phenylenediamines, p-aminophenols, 2,4,5,6-tetraamiopyrimidines and / or 4,5- diaminopyrazoles.
- Oxidation dye precursors from the group of p-phenylenediamines are oxidation dye precursors which can be based on a p-phenylenediamine unit or are the derivatives thereof. This means that the p-phenylenediamine unit of the oxidation dye precursors can also be mono- or polysubstituted, the premise being that the substitution must be such that even an oxidative coupling reaction with the resorcinols (or the additionally contained couplers) to the dye can take place.
- Particularly suitable oxidation dye precursors from the group of p-phenylenediamines are p-phenylenediamine itself, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, 2- (1, 2-dihydroxyethyl) -p-phenylenediamine, N, N- Bis (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1 H -imidazol-1-yl) propyl] amine , N, N'-bis- (2-hydroxyethyl) -N, N'-bis (4-aminophenyl) -1,3-diamino-propan-2-ol, 1,3-bis- (2,5-) diaminophenoxy) - propan-2-ol, N, N'-bis (4-a
- Very particularly suitable oxidation dye precursors from the group of p-phenylenediamines are p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylene - Diamine, 2-methoxymethyl-p-phenylenediamine and / or the physiologically acceptable salts of these compounds.
- Preferred physiologically acceptable salts of p-toluenediamine are in particular the hydrochlorides (monohydrochloride x HCl, or dihydrochloride x 2 HCl), the sulfate (x H 2 SO 4) and the hydrobromides (monohydrobromide x HBr, or dihydrobromide x 2 HBr) of the compound.
- hydrochlorides monohydrochloride x HCl, or dihydrochloride x 2 HCl
- sulfate x H 2 SO 4
- hydrobromides monohydrobromide x HBr, or dihydrobromide x 2 HBr
- Preferred physiologically acceptable salts of 2- (2,5-diaminophenyl) ethanol are in particular the hydrochlorides (monohydrochloride x HCl, or dihydrochloride x 2 HCl), the sulfate (x H2SO4) and the hydrobromides (monohydrobromide x HBr, or dihydrobromide x 2 HBr ) the connection.
- hydrochlorides monohydrochloride x HCl, or dihydrochloride x 2 HCl
- x H2SO4 the hydrobromides
- N, N-bis (2-hydroxyethyl) -p-phenylenediamine is a compound of the formula
- Preferred physiologically tolerated salts of N, N-bis (2-hydroxyethyl) -p-phenylenediamine are in particular the hydrochlorides (monohydrochloride x HCl, or dihydrochloride x 2 HCl), the sulfate (x H2SO4) and the hydrobromides (monohydrobromide x HBr, or dihydrobromide x 2 HBr) of the compound.
- the hydrochlorides monohydrochloride x HCl, or dihydrochloride x 2 HCl
- x H2SO4 the sulfate
- hydrobromides monohydrobromide x HBr, or dihydrobromide x 2 HBr
- 2-methoxymethyl-p-phenylenediamine is a compound of the formula (VII)
- Preferred physiologically acceptable salts of 2-methoxymethyl-p-phenylenediamine are in particular the hydrochlorides (monohydrochloride x HCl, or dihydrochloride x 2 HCl), the sulfate (x H2SO4) and the hydrobromides (monohydrobromide x HBr, or dihydrobromide x 2 HBr) Connection.
- hydrochlorides monohydrochloride x HCl, or dihydrochloride x 2 HCl
- x H2SO4 the sulfate
- hydrobromides monohydrobromide x HBr, or dihydrobromide x 2 HBr
- Oxidation dye precursors from the group of the p-aminophenols are oxidation dye precursors, which can be based on a p-aminophenol unit or are the derivatives thereof. This means that the p-aminophenol unit of the oxidation dye precursors can also be mono- or polysubstituted, the premise being that the substitution must be such that even an oxidative coupling reaction with the resorcinols (or the additionally contained couplers) to the dye can take place.
- Particularly suitable oxidation dye precursors from the group of p-aminophenols are p-aminophenol itself, 4-amino-3-methylphenol, bis (2-hydroxy-5-aminophenyl) methane and / or the physiologically tolerated salts of these compounds.
- Preferred physiologically acceptable salts of p-aminophenol are in particular the hydrochlorides (monohydrochloride x HCl), the sulfate (x H2SO4) and the hydrobromide.
- Preferred physiologically acceptable salts of 4-amino-3-methyphenol are in particular the hydrochlorides (monohydrochloride x HCl), the sulfate (x H2SO4) and the hydrobromide.
- Preferred physiologically acceptable salts of bis (2-hydroxy-5-aminophenyl) methane are in particular the hydrochlorides (monohydrochloride x HCl), the sulfate (x H2SO4) and the hydrobromide.
- Oxidation dye precursors from the group of 2,4,5,6-tetraaminopyrimidines are oxidation dye precursors which can be based on a 2,4,5,6-tetraamiopyrimidine moiety or are the derivatives thereof. This means that the 2, 4, 5, 6-tetraamiopyrimidine moiety of the oxidation dye precursors can also be mono- or polysubstituted, the premise being that the substitution must be such that even an oxidative coupling reaction with the resorcinols (or the additionally contained couplers) to the dye can take place.
- a particularly suitable oxidation dye precursors from the group of 2,4,5,6-tetraaminopyrimidines is the 2,4,5,6-tetraaminopyrimidine itself or its physiologically tolerated salts.
- Oxidation dye precursors from the group of 4,5-diaminopyrazoles are oxidation dye precursors which can be based on a 4,5-diaminopyrazole unit or are the derivatives thereof.
- the 4,5-diaminopyrazole unit of the oxidation dye precursors can also be monosubstituted or polysubstituted, the premise being that the substitution must be such that one more oxidative Coupling reaction with the resorcinols (or the additional couplers contained) can take place to the dye.
- a particularly suitable oxidation dye precursors from the group of 4,5-diaminopyrazoles is 4,5-diamino-1- (2-hydroxyethyl) pyrazole itself or its physiologically tolerated salts.
- Preferred physiologically acceptable salts of 4,5-diamino-1- (2-hydroxyethyl) -1H-pyrazole are in particular the hydrochlorides (monohydrochloride x HCl, or dihydrochloride x 2 HCl), the sulfate (x H2SO4) and the hydrobromides (monohydrobromide x HBr, or dihydrobromide x 2 HBr) of the compound.
- hydrochlorides monohydrochloride x HCl, or dihydrochloride x 2 HCl
- x H2SO4 the hydrobromides
- 4,5-diamino-1- (2-hydroxyethyl) -1H-pyrazole sulfate formula (Villa)).
- oxidation dyes of the developer type (A2) are selected from the group of p-phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, N, N-bis- (2-hydroxyethyl) -p- phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazol-1-yl) propyl] amine, bis (2-hydroxybenzyl) 5-aminophenyl) methane, p-aminophenol, 4-amino-3-methylphenol, 4,5-diamino-1- (2-hydroxyethyl) pyrazole, 2,4,5,6-tetraaminopyrimidine, 4-
- the salts of the oxidation dyes of the developer type (A2) must be physiologically compatible.
- Physiologically acceptable in this context means for use in the cosmetic agent (ie for use on human hair and human skin) suitable.
- Particularly preferred physiologically acceptable salts are the hydrochlorides, the hydrobromides, the hemisulfates, the sulfates, the p-toluenesulfonates, the benzenesulfonates, the acetates, the lactates and / or the tartrates of the oxidation type dyes (A2).
- hydrochlorides monohydrochloride x HCl or dihydrochloride x 2 HCl
- sulfates x H2SO4
- hydrobromides monohydrobormides x HBr or dihydrobromides x 2 HBr
- a multi-component packaging unit (kit-of-parts) according to the invention is characterized in that the first preparation (A) contains one or more oxidation dye precursors of the developer type (A2) which are selected from the group consisting of p- Phenylenediamine, p-toluenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3 -methylphenyl) -N- [3- (1 H -imidazol-1-yl) propyl] amine, bis (2-hydroxy-5-aminophenyl) methane, p-aminophenol, 4-amino-3-methylphenol, 4, 5-diamino-1 - (2-hydroxyethyl) pyrazole, 2,4,5,6-tetraamin
- the oxidation dye precursors of the developer type (A2) are contained in certain quantitative ranges in the preparation (A). Particularly intensive dyeings are obtained when the first preparation (A) contains one or more oxidation dye precursors of the developer type (A2) in a total amount of from 0.1 to 2.5% by weight, preferably from 0.2 to 2.3% by weight. %, more preferably from 0.6 to 1, 7 wt .-% and particularly preferably from 0.9 to 1, 1 wt .-%.
- the basis for calculating these amounts in% by weight is the total weight of all the oxidation dye precursors of the developer type from group (A2), which is related to the total weight of the preparation (A).
- a multi-component packaging unit (kit-of-parts) according to the invention is characterized in that the first preparation (A) - based on the total weight of the preparation (A) - one or more oxidation dye precursors of the developer type (A2) in a total amount of from 0.1 to 2.5% by weight, preferably from 0.2 to 2.3% by weight, more preferably from 0.6 to 1.7% by weight and particularly preferably from 0, Contains 9 to 1, 1 wt .-%.
- a very central and essential feature of the present invention is that, in the preparation (A), the molar ratio of all resorcinol derivatives (A1) to all the developer-type oxidation dye precursors (A2), i. the molar ratio (A1) / (A2) is at a value of at least 1.2.
- the resorcinol derivatives (A1) are used in an at least 1.2-fold molar excess compared to the developer-type oxidation dye precursors (A2).
- the resorcinol derivatives (A1) contained in the molar excess ensure that in addition to the dyeing of the keratin fibers, which is achieved by reaction of the resorcinols (A1) with the oxidation dye precursors of the developer type (A2) to form dyes, smoothing is also achieved can be. Without being limited to this theory, it is assumed that the smoothing is caused by the excess resorcinol (A1), since the resorcins (A1), which are not consumed in the dye-forming reaction, can act as swelling agents, whereby the shape of the keratin fibers can be permanently influenced.
- the molecular weight (unit g / mol) of a compound is defined as mass (unit g) per amount of substance (unit mol).
- the quantity of substance is understood to mean the quantity of a substance portion on the basis of the number of particles contained therein.
- the unit of the amount of substance is the basic unit mol (mol or mmol).
- the quantitative ratio of the resorcinols (A1) to the developer-type oxidation dye precursors (A2) is defined as a molar ratio since the developer-type oxidation dye precursors (A2) react with a certain number of resorcinol molecules (A1).
- the preparation (B) contains no oxidation dye precursors (ie neither compounds from the group (A1) nor compounds from the group (A2)), the molar ratio (A1) / (A2) in the preparation (A) also corresponds to the molar ratio (A1) / (A2) in the ready-to-use forming agent prepared by mixing the preparations (A) and (B).
- the molar amount of the compounds (A1) and (A2) contained in the preparation (A) can be respectively
- the preparation contains (A)
- the preparation contains (A)
- the preparation contains (A)
- the molar ratio (A1) / (A2) in the ready-to-use agent (which is a mixture of the
- Preparations (A) and (B) is also 7.83.
- the resorcinol derivatives (A1) In order for the resorcinol derivatives (A1) to cause both reshaping and staining of the keratin fibers, they must be contained in the preparation (A) in an at least 1.2-fold molar excess as compared to the developer-type oxidation dyes (A2).
- the molar ratio of all the resorcinol derivatives (A1) present in the composition to all of the developer-type oxidation dyes (A2) i. the molar ratio (A1) / (A2), at a value of 1, 3 to 60.0, preferably from 1, 5 to 50.0, preferably from 2.0 to 45.0, more preferably from 4.0 to 35.0 and more preferably from 7.0 to 32.0.
- a multi-component packaging unit (kit-of-parts) according to the invention is therefore characterized in that the molar ratio of all resorcinol derivatives (A1) contained in the preparation (A) to all in the preparation (A) developer-type oxidation dye precursors (A2), ie the molar ratio (A1) / (A2), at a value of 1.3 to 60.0, preferably from 1.5 to 50.0, more preferably from 2.0 to 45.0, even more preferably from 4, 0 to 35.0 and more preferably from 7.0 to 32.0.
- the preparation (A) may additionally also contain one or more couplers which are structurally different from the resorcinol derivatives (A1). Additional couplers can be used to modify the desired shade.
- Coupler components do not form a significant color within the framework of the oxidative dyeing alone, but always require the presence of developer components. Coupler components permit at least one substitution of a chemical residue of the coupler by the oxidized form of the developer component. Covalent bonds form between coupler and developer components.
- coupler component suitable according to the invention preference is given to selecting at least one compound from one of the following classes:
- o-aminophenol derivatives such as o-aminophenol
- Naphthalene derivatives having at least one hydroxy group having at least one hydroxy group
- Pyrazolone derivatives such as 1-phenyl-3-methylpyrazol-5-one,
- Morpholine derivatives such as, for example, 6-hydroxybenzomorpholine or 6-aminobenzomorpholine,
- the additional couplers form very intense colors in combination with the oxidation dye precursors from group (A2).
- additional couplers which are selected from the group of 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4 -chloro-2-methylphenol, 5- (2-hydroxyethyl) amino-2-methylphenol, 2,4-dichloro-3-aminophenol, 2-aminophenol, 3-phenylenediamine, 2- (2,4-diaminophenoxy) ethanol, 1, 3-bis (2,4-diaminophenoxy) propane, 1-methoxy
- a multi-component packaging unit (kit-of-parts) according to the invention is characterized in that the preparation (A) additionally contains at least one or more couplers from the group formed from 3-aminophenol, 5-amino-2 methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4-chloro-2-methylphenol, 5- (2-hydroxyethyl) amino-2-methylphenol, 2 , 4-dichloro-3-aminophenol, 2-aminophenol, 3-phenylenediamine, 2- (2,4-diaminophenoxy) ethanol, 1, 3-bis (2,4-diaminophenoxy) propane, 1-methoxy-2-amino 4- (2-hydroxyethylamino) benzene, 1, 3-bis (2,4-diaminophenyl) propane, 2,6-bis (2'-hydroxyethylamino) -1-methylbenzene, 2 - ( ⁇ 3
- the preparation (A) may in principle additionally one or more coupler components from the aforementioned group in a total amount of 0.001 to 3.0 wt .-%, preferably from 0.025 to 1, 5 wt .-%, more preferably from 0.05 to 1 , 0 wt .-% and particularly preferably from 0.1 to 0.5 wt .-% - based on the total weight of the preparation (A) - included.
- the preparation (A) may additionally contain at least one substantive dye from the group of anionic, nonionic and / or cationic dyes.
- nonionic substantive direct dyes from the group HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC HC Red 7, HC Red 10, HC Red 1, HC Red 1, HC Red BN, HC Blue 2, HC Blue 1 1, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, 1, 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1, 4-bis (2-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- ( 2-hydroxyethyl) aminophenol, 2- (2-hydroxyethyl) amino-4,6-dinitrophenol, 4 - [(2-hydroxyethyl) amino] -3-nitro-1-methylbenzene, 1-amino-4- (2 - hydroxyethyl) amino-5-chloro-2-nitrobenzene, 4-amino-3-nitrophenol, 1- (2'-
- Suitable cationic substantive dyes are cationic triphenylmethane dyes such as Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14, aromatic systems substituted with a quaternary nitrogen group such as Basic Yellow 57, Basic Red 76, Basic Blue 99 , Basic Brown 16 and Basic Brown 17, cationic anthraquinone dyes such as HC Blue 16 (Bluequat B) and direct dyes containing a heterocycle having at least one quaternary nitrogen atom, in particular Basic Yellow 87, Basic Orange 31 and Basic Red 51
- the cationic substantive dyes sold under the trademark Arianor are also suitable cationic substantive dyes according to the invention.
- anionic dyes or acid dyes for example, one or more compounds from the following group can be selected: Acid Yellow 1 (D & C Yellow 7, Citronin A, Ext. D & C Yellow No. 7, Japan Yellow 403, CI 10316, COLIPA n ° B001) Acid Yellow 3 (COLIPA n ° C 54, D & C Yellow N ° 10, Quinoline Yellow, E104, Food Yellow 13), Acid Yellow 9 (CI 13015), Acid Yellow 17 (CI 18965), Acid Yellow 23 (COLIPA n C 29, Covacap Jaune W 1 100 (LCW), Sicovit Tartrazine 85 E 102 (BASF), Tartrazine, Food Yellow 4, Japan Yellow 4, FD & C Yellow No.
- Acid Yellow 36 (CI 13065), Acid Yellow 121 (Cl 18690), Acid Orange 6 (CI 14270), Acid Orange 7 (2-naphthol orange, Orange II, Cl 15510, D & C Orange 4, COLIPA n ° C015), Acid Orange 10 (Cl 16230, Orange G sodium salt ), Acid Orange 1 1 (Cl 45370), Acid Orange 15 (Cl 50120), Acid Orange 20 (Cl 14600), Acid Orange 24 (BROWN 1, CI 20170, KATSU201, nosodiumsalt, Brown No.201, RESORCIN BROWN, ACID ORANGE 24, Japan Brown 201, D & C Brown No.1), Acid Red 14 (C .1.14720), Acid Red 18 (E124, Red 18, Cl 16255), Acid Red 27 (E 123, Cl 16185, C Red 46, Fast Red D, FD & C Red No.2, Food Red 9, Naphthol Red S), Acid Red 33 (Red 33, Fuchsia Red, D & C Red 33, CI
- Acid Blue 50 (Cl 50325), Acid Blue 1 (Patent Blue, Cl 42045), Acid Blue 3 (Patent Blue V, Cl 42051), Acid Blue 7 (Cl 42080), Acid Blue 104 (Cl 42735 ), Acid Blue 9 (E 133, Patent Blue AE, Amidoblue AE, Erioglaucin A, Cl 42090, Cl.
- Food Blue 2 Acid Blue 2 (CI 62045), Acid Blue 74 (E 132, CI 73015), Acid Blue 80 (CI 61585), Acid Green 3 (CI 42085, Foodgreenl), Acid Green 5 (CI 42095), Acid Green 9 (C.1.42100), Acid Green 22 (C.1.42170), Acid Green 25 (Cl 61570, Japan Green 201, D & C Green No.
- Acid Green 50 (Brilliant Acid Green BS, Cl 44090, Acid Brilliant Green BS, E 142), Acid Black 1 (Black n ° 401, Naphthalene Black 10B, Amido Black 10B, Cl 20 470, COLIPA n ° B15), Acid Black 52 (Cl 1571 1), Food Yellow 8 (Cl 14270), Food Blue 5, D & C Yellow 8, D & C Green 5, D & C Orange 10, D & C Orange 1 1, D & C Red 21, D & C Red 27, D & C Red 33, D & C Violet 2 and / or D & C Brown 1.
- the multicomponent packaging unit (kit-of-parts) according to the invention furthermore comprises the preparation (B) prepared separately from the preparation (A).
- the preparation (B) contains hydrogen peroxide in a cosmetic carrier (B1). By reacting the hydrogen peroxide with the oxidation dye precursors, the dyes form in an oxidative dyeing process. To prevent premature reaction, the compounds (A1) and (A2) can not be stored together with the hydrogen peroxide.
- hydrogen peroxide itself is used as the aqueous solution in the preparation (B).
- concentration of a hydrogen peroxide solution in the preparation (B) is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6 to 12 wt .-% solutions are used in water.
- Preparations (B) preferred according to the invention are characterized in that they contain from 0.1 to 6.0% by weight, preferably from 0.15 to 5.0% by weight, more preferably from 0.2 to 4.5% by weight. % and very particularly preferably from 0.3 to 4.2% by weight of hydrogen peroxide, in each case based on the total weight of the preparation (B).
- a multi-component packaging unit (kit-of-parts) is therefore characterized in that the second preparation (B) - based on the total weight of the preparation (B) - hydrogen peroxide in an amount of 0, 1 to 12.0 wt .-%, preferably from 0, 15 to 5.0 wt .-%, more preferably from 0.2 to 4.5 wt .-% and most preferably from 0.3 to 4.2 Wt .-% contains.
- the ready-to-use forming and coloring agent ie by application of the mixture of the preparations (A) and (B)
- keratinic fibers can be both oxidatively colored and permanently deformed.
- the multi-component packaging units are particularly preferred, which are characterized in that the preparation (A) is free of reducing agents.
- the preparation (B) contains as the oxidizing agent hydrogen peroxide, so that the addition of reducing agents to the preparation (B) would cause undesirable reactions between the oxidizing agent and the reducing agent and therefore also not indicated.
- a preparation (A) which is free from reducing agents is understood to mean a preparation whose total content of reducing agents selected from the group consisting of thioglycolic acid, thiolactic acid, cysteine and the salts of these compounds, based on the total weight of the preparation (A), is less than 1 , 0 wt .-%, preferably below 0.5 wt .-%, more preferably below 0.1 wt .-% and particularly preferably below 0.05 wt .-%.
- a multi-component packaging unit (kit-of-parts) according to the invention is characterized in that the first preparation (A) - based on the total weight of the preparation (A) - reducing substances selected from the group consisting of thioglycolic acid, thiolactic acid , Cysteine and the salts of these compounds in a total amount of less than 1, 0 wt .-%, preferably less than 0.5 wt .-%, more preferably less than 0, 1 wt .-% and particularly preferably less contains as 0.05 wt .-%.
- the preparation (A) may contain small amounts of reducing agents from the group of sulfites (e.g., sodium sulfite, sodium bisulfite, ammonium sulfite, potassium sulfite, etc.) or ascorbic acid.
- reducing agents from the group of sulfites (e.g., sodium sulfite, sodium bisulfite, ammonium sulfite, potassium sulfite, etc.) or ascorbic acid.
- the amounts used of these reducing agents are below 1, 0 wt .-%, preferably below 0.5 wt .-%, even more preferably below 0, 1 wt .-% (each calculated as the total weight of the reducing agent from the group the sulfites and ascorbic acid based on the total weight of the preparation (A)).
- these reducing agents especially in these small amounts used - do not reshape the keratinic fibers, but are merely intended to prevent an unattractive discoloration of the preparation (A) caused by the reaction of the oxidation dye precursors (A2) with atmospheric oxygen. In order to completely minimize hair damage, it may be advantageous to dispense with these reducing agents as well.
- a multi-component packaging unit (kit-of-parts) is characterized in that the first preparation (A) - based on the total weight of the preparation (A) - reducing substances from the group consisting of thioglycolic acid, thiolactic acid, cysteine and the salts of these compounds, sodium sulphite, sodium bisulphite, ammonium sulphite, ammonium bisulphite, potassium sulphite and potassium bisulphite in a total amount of less than 1.0% by weight, preferably of less than 0.5% by weight. %, more preferably less than 0, 1 wt .-% and particularly preferably less than 0.05 wt .-%.
- the preparation (A) and / or the preparation (B) contains at least one further swelling agent.
- the swelling agent is preferably a compound from the group of urea and urea derivatives, guanidine and its derivatives, arginine and its derivatives, water glass, imidazole and its derivatives, histidine and its derivatives, benzyl alcohol, glycerol, glycol and glycol ethers, propylene glycol and propylene glycol, for example propylene glycol monoethyl ether , Carbonates, bicarbonates, diols and triols, and in particular 1, 2-diols and 1, 3-diols such as 1, 2-propanediol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-dodecanediol, 1, 3-propanediol, 1, 6-hexanediol, 1, 5-p
- a particularly advantageous hair straightening and particularly advantageous dyeing results by the use of a swelling agent from the group of urea (urea), glycerol (propane-1, 2,3-triol), sorbitol (D-glucitol) and / or pyrrolidonecarboxylic acid (5-oxopyrrolidine -2-carboxylic acid), in particular urea.
- a swelling agent from the group of urea (urea), glycerol (propane-1, 2,3-triol), sorbitol (D-glucitol) and / or pyrrolidonecarboxylic acid (5-oxopyrrolidine -2-carboxylic acid), in particular urea.
- urea urea
- glycerol propane-1, 2,3-triol
- sorbitol D-glucitol
- pyrrolidonecarboxylic acid 5-oxopyrrolidine -2-carboxylic acid
- the proportion by weight of the swelling agent in the total weight of the preparation (A) or the preparation (B) is preferably 0.2 to 15 wt .-%, preferably 1, 0 to 12 wt .-% and in particular 2.0 to 10 wt. %.
- a multi-component packaging unit (kit-of-parts) according to the invention is therefore characterized in that the preparation (A) and / or the preparation (B) comprises at least one swelling agent, preferably from the group consisting of urea (urea). , Glycerol (propane-1,2,3-triol), sorbitol (D-glucitol) and / or pyrrolidonecarboxylic acid (5-oxopyrrolidine-2-carboxylic acid).
- urea urea
- Glycerol propane-1,2,3-triol
- sorbitol D-glucitol
- pyrrolidonecarboxylic acid 5-oxopyrrolidine-2-carboxylic acid
- the preparations (A) and / or (B) may contain further bleaching power boosters to enhance the lightening effect, such as, for example, tetraacetylethylenediamine (TAED), 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT).
- TAED tetraacetylethylenediamine
- DADHT 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine
- Tetraacetylglycoluril (TAGU), N-nonanoylsuccinimide (NOSI), n-nonanoyl or isononanoyloxybenzenesulphonate (n- or i-NOBS), phthalic anhydride, triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran, and carbonate salts or Bicarbonate salts, in particular, ammonium hydrogencarbonate, ammonium carbonate, sodium hydrogencarbonate, disodium carbonate, potassium hydrogencarbonate, dipotassium carbonate and calcium carbonate; and nitrogen-containing heterocyclic bleach boosters such as 4-acetyl-1-methylpyridinium p-toluenesulfonate, 2-acetyl-1-methylpyridinium p-toluenesulfonate, and N -Methyl-3,4-dihydroisoquinolinium p-tolu
- the preparations (A) and / or (B) may additionally also contain at least one SiO 2 compound, such as silicic acid or silicates, in particular water glasses, be added.
- the SiO 2 compound may in this case be present in the dyeing preparation (A) and / or in the oxidizing agent preparation (B).
- the S1O2 compounds in amounts of 0.05 wt .-% to 15 wt .-%, more preferably in amounts of 0.15 wt .-% to 10 wt .-% and most preferably in Amounts of from 0.2% to 5% by weight, based in each case on the total weight of the dyeing preparation (A) or on the total weight of the oxidizing agent preparation (B).
- compositions (A) and / or (B) may further comprise additional active ingredients, auxiliaries and additives in order to improve the dyeing or brightening performance and to adjust further desired properties of the compositions.
- the ready-to-use colorants are provided as a liquid preparation and the agents therefore optionally additionally added a further surfactant, said surfactants depending on the field of application as surfactants or as emulsifiers: They are preferably anionic, zwitterionic, amphoteric and nonionic surfactants and emulsifiers selected.
- Agents suitable according to the invention are characterized in that the agent additionally contains at least one anionic surfactant.
- Preferred anionic surfactants are fatty acids, alkyl sulfates, alkyl ether sulfates and ether carboxylic acids having 10 to 20 carbon atoms in the alkyl group and up to 16 glycol ether groups in the molecule.
- Agents suitable according to the invention are characterized in that the agent additionally contains at least one zwitterionic surfactant.
- Preferred zwitterionic surfactants are betaines, N-alkyl- ⁇ , ⁇ -dimethylammonium glycinates, N-acyl-aminopropyl-N, N-dimethylammoniumglycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazoline.
- a preferred zwitterionic surfactant is known by the INCI name Cocamidopropyl Betaine.
- Agents suitable according to the invention are characterized in that the agent additionally contains at least one amphoteric surfactant.
- Preferred amphoteric surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids.
- Particularly preferred amphoteric surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 -acylsarcosine.
- the agents contain other, nonionic surfactants.
- Preferred nonionic surfactants are alkyl polyglycosides and alkylene oxide adducts of fatty alcohols and fatty acids with in each case 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid. Preparations having excellent properties are also obtained if they contain fatty acid esters of ethoxylated glycerol as nonionic surfactants.
- the nonionic, zwitterionic or amphoteric surfactants are used in proportions of from 0.1 to 45% by weight, preferably from 1 to 30% by weight and very particularly preferably from 1 to 15% by weight, based on the total amount of ready-to-use agents.
- the ready-to-use color-change agents may also contain at least one thickener. With regard to these thickeners, there are no fundamental restrictions. Both organic and purely inorganic thickening agents can be used.
- Suitable thickeners are anionic, synthetic polymers, cationic, synthetic polymers, naturally occurring thickeners, such as nonionic guar gums, scleroglucan gums or xanthan gums, gum arabic, ghatti gum, karaya gum, tragacanth gum, carrageenan gum, agar agar, Locust bean gum, pectins, alginates, starch fractions and derivatives such as amylose, amylopectin and dextrins, as well as cellulose derivatives such as methylcellulose, carboxyalkylcelluloses and hydroxyalkylcelluloses, nonionic fully synthetic polymers such as polyvinyl alcohol or polyvinylpyrrolidinone; and inorganic thickening agents, in particular phyllosilicates such as bentonite, especially smectites, such as montmorillonite or hectorite.
- thickening agents in particular phyllosilicates such as benton
- the colorants in particular if they additionally contain hydrogen peroxide, contain at least one stabilizer or complexing agent.
- Particularly preferred stabilizers are phenacetin, alkali benzoates (sodium benzoate) and salicylic acid.
- all complexing agents of the prior art can be used.
- Preferred complexing agents according to the invention are nitrogen-containing polycarboxylic acids, in particular EDTA and EDDS, and phosphonates, in particular 1-hydroxyethane-1, 1-diphosphonate (HEDP) and / or ethylenediamine tetramethylenephosphonate (EDTMP) and / or diethylenetriaminepentamethylenephosphonate (DTPMP) or their sodium salts.
- the agents according to the invention may contain further active ingredients, auxiliaries and additives, for example nonionic polymers such as, for example, vinylpyrrolidinone / vinyl acrylate copolymers, polyvinylpyrrolidinone, vinylpyrrolidinone / vinyl acetate copolymers, polyethylene glycols and polysiloxanes; additional silicones, such as volatile or nonvolatile, straight-chain, branched or cyclic, crosslinked or uncrosslinked polyalkylsiloxanes (such as dimethicones or cyclomethicones), polyarylsiloxanes and / or polyalkylarylsiloxanes, in particular polysiloxanes with organofunctional groups, such as substituted or unsubstituted amines (amodimethicones), carboxyl, Alkoxy and / or hydroxyl groups (dimethicone copolyols), linear polysiloxane (A) polyoxyalkylene (B) block copo
- the choice of these other substances will be made by those skilled in the art according to the desired properties of the agents.
- additional active ingredients and auxiliaries are preferably used in the agents according to the invention in amounts of from 0.0001 to 25% by weight, in particular from 0.0005 to 15% by weight, based in each case on the total weight of the dyeing preparation (A) and / or the oxidizing agent preparation (B) used.
- the staining and reshaping of the keratinic fibers may be at pH's in the range of 2 to 12, but dyeing and reshaping in the alkaline range is preferred.
- Essential for the dyeing and conversion result here is the pH of the ready-to-use agent, i. the mixture of preparations (A) and (B).
- the preparation (B) containing the oxidizing agent hydrogen peroxide is adjusted to an acidic pH of from 1.0 to 6.0, preferably from 2.0 to 5.0.
- the preparation (A) is preferably adjusted to an alkaline pH of from 7.0 to 11.5, preferably from 8.0 to 10.5.
- the pH of the mixture of the preparations (A) and (B) is preferably also in the alkaline range of 7.5 to 10.5.
- inorganic acids for example, mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid, preferably in their water-diluted form can be used.
- organic acids can also be used in the formulations according to the invention. Typical representatives of organic acids are aliphatic mono- and dicarboxylic acids such as acetic acid, propionic acid, oxalic acid and 1, 3-propanedioic acid and aromatic carboxylic acids such as benzoic acid.
- organic acids according to the invention are hydroxycarboxylic acids such as glycolic acid, citric acid, tartaric acid, malic acid and lactic acid. Also unsaturated mono- or dicarboxylic acids such as fumaric acid or ⁇ -ketocarboxylic acids such as pyruvic acid (2-oxopropionic acid) are according to the invention.
- hydroxycarboxylic acids such as glycolic acid, citric acid, tartaric acid, malic acid and lactic acid.
- unsaturated mono- or dicarboxylic acids such as fumaric acid or ⁇ -ketocarboxylic acids such as pyruvic acid (2-oxopropionic acid) are according to the invention.
- low odor acids approved for use in cosmetics are most suitable for the development of hair treatment products with good dyeing performance.
- the alkalizing agents which can be used according to the invention for setting the preferred pH values-in particular the pH of the preparation (A) - can be selected from the group consisting of ammonia, alkanolamines, basic amino acids, and inorganic alkalizing agents, such as (earth) alkali metal hydroxides. Earth) alkali metal metasilicates, (earth) alkali metal phosphates and (earth) alkali metal hydrogen phosphates.
- Preferred inorganic alkalizing agents are magnesium carbonate, sodium hydroxide, potassium hydroxide, sodium silicate and sodium metasilicate.
- Organic alkalizing agents which can be used according to the invention are preferably selected from monoethanolamine, 2-amino-2-methylpropanol and triethanolamine.
- the basic amino acids which can be used as alkalizing agents according to the invention are preferably selected from the group formed from arginine, lysine, ornithine and histidine, more preferably arginine.
- further preferred agents according to the invention are characterized in that they additionally contain an organic alkalizing agent.
- An embodiment of the first subject of the invention is characterized in that the agent additionally contains at least one alkalizing agent which is selected from the group consisting of ammonia, alkanolamines and basic amino acids, in particular ammonia, monoethanolamine and arginine or its compatible salts.
- the pH values measured for the purposes of this invention are pH values measured at a temperature of 22 ° C.
- glass electrodes are particularly suitable, which can be designed, for example, in the form of a combination electrode.
- the preparations of the multicomponent packaging unit (kit-of-parts) essential to the invention are the preparations (A) and (B), since their mixing and application is responsible for the dyeing and transformation results of the keratin fibers.
- the multi-component packaging unit may also comprise further preparations, such as, for example, a third conditioner preparation (C) which may contain care ingredients such as cationic polymers or cationic surfactants.
- a multi-component packaging unit according to the invention comprises precisely these two preparations (A) and (B) and does not contain a third preparation which would be applied to the keratinic fibers as pre- or post-treatment agent .
- a multi-component packaging unit (kit-of-parts) according to the invention is characterized in that it comprises two separately prepared preparations (A) and (B).
- the multi-component packaging unit comprises exactly the two separately prepared preparations (A) and (B) and no further preparation (C).
- the multicomponent packaging units according to the invention can be used in processes for the simultaneous shaping and dyeing of keratinic fibers, in particular human hair.
- a second aspect of the present invention is a method of reshaping and staining human hair, comprising the following steps:
- step (II) Application of the ready-to-use forming and production process prepared in step (I)
- the ready-to-use forming and coloring agent preparations (A) and (B) in a weight ratio of 1:10 to 10: 1 are mixed together. It is particularly advantageous with regard to optimum shaping and dyeing if the preparations (A) and (B) are in a quantitative ratio (A) / (B) of 3: 1 to 1: 3, preferably 2: 1 to 1: 2 and more preferably from 1, 5: 1 to 1: 1, 5 are mixed.
- a method according to the invention is therefore characterized in that in step (I) the preparations (A) and (B) in a quantitative ratio (A) / (B) of 3: 1 to 1: 3, preferably from 2 : 1 to 1: 2 and more preferably from 1, 5: 1 to 1: 1, 5 are mixed.
- the ready-to-use agent ie, the mixture of formulations (A) and (B)
- the heat supply can be done by an external heat source, such as warm air of a hot air blower, as well as, especially in an application to the living subjects, by the body temperature of the subject. In the latter case, the treated batch is usually covered with a hood.
- An action phase or mechanical deformation at room temperature is also according to the invention.
- the temperature during the exposure time or during the forming between 20 ° C and 80 ° C, in particular between 30 ° C and 65 ° C.
- a method according to the invention is therefore characterized in that in step (III) the mechanical deformation of the hair takes place at a temperature of 20 to 80 ° C., preferably at a temperature of 30 to 65 ° C.
- the mechanical deformation carried out in step (III) of the method according to the invention may be a curling or curling of the hair, this being achieved, for example, by winding the hair on winder or papillote before application of the agent and then applying the agent to the winder located hair acts.
- the mechanical deformation is a smoothing of the hair, for example, by combing bwz. Smooth hair can be done with a comb or a brush.
- a method according to the invention is therefore characterized in that in step (III) the mechanical deformation is a smoothing of the hair which takes place by combing or smoothing the hair with a comb or with a brush.
- the ready-to-use forming and coloring agent may be applied to the hair for a period of 5 to 60 minutes, preferably for 10 to 55 minutes, and more preferably for 25 to 50 minutes.
- the forming and coloring agent in step (IV) is rinsed with water or a cleaning agent from the hair.
- a cleaning agent can be used in particular commercial shampoo, in particular then can be dispensed with the detergent and the rinsing can be done with water when the forming and dyeing agent has a strong surfactant-containing carrier.
- the hair may then be dried in step (V), either at room temperature or with the aid of a heat hood or a hair dryer
- the inventive method is characterized by the steps (I) to (IV), as well as by the optional step (V).
- the exact sequence of the steps can be varied as desired by the user.
- a method according to the invention is characterized in that the sequence of steps in the method is the following: step (I) followed by step (II) followed by step (III) followed by step (IV) from step (V)
- step (II) Application of the ready-to-use forming and production process prepared in step (I)
- a method according to the invention is characterized in that the sequence of steps in the method is the following: step (I), followed by step (II), followed by step (IV), followed by step (III), followed by step (V).
- step (II) Application of the ready-to-use forming and production process prepared in step (I)
- This second embodiment is of greater comfort to the user, since the mechanical smoothing (for example, by combing or smoothing with a comb or a brush) can also be done after the ready-dyeing and forming agent has been rinsed out of the hair again.
- the mechanical smoothing for example, by combing or smoothing with a comb or a brush
- the resorcinol derivatives (A1) which have diffused into the hair and are present in excess within the fiber also cause a smoothing of the hair when the transformation and coloring agent itself had already been rinsed off again by the hair.
- Another object of the present invention is therefore the use of an agent which is prepared by mixing two separately formulated preparations (A) and (B), for reshaping and dyeing of human hair, wherein the preparations (A) and (B) in
- Another object is the use of resorcinol, 2-methylresorcinol and / or 4-
- Chlororesorcinol in an oxidative hair dye for hair remodeling Chlororesorcinol in an oxidative hair dye for hair remodeling.
- the preparation (A) was in each case mixed with the preparations (B) in a ratio of 1: 1.
- the strands used in these experiments were curly hair strands of the same length.
- Each of these ready-to-use agents was applied in each case to a curly strand of hair (Kerling 6-0) (4 g of dye per 1 g of hair), left there for 45 minutes and smoothed several times with a comb. Then the tress was rinsed with warm water, combed again with a comb and dried with a hair dryer.
- each strand was examined against the background of a scaled template, the scaling of the length of the hair strand was determined. Subsequently, the strands were washed with a shampoo, and dried hanging in a climatic chamber. After drying, the strands were reassessed against the background of a scaled template, and scaling was used to determine the length of the hair strand again.
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102014226320.4A DE102014226320A1 (en) | 2014-12-17 | 2014-12-17 | Resorcinol derivatives in agents for the simultaneous remodeling and staining of keratinic fibers |
PCT/EP2015/076790 WO2016096283A1 (en) | 2014-12-17 | 2015-11-17 | Resorcinol derivatives in compositions for simultaneous reshaping and colouring of keratinous fibres |
Publications (2)
Publication Number | Publication Date |
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EP3233033A1 true EP3233033A1 (en) | 2017-10-25 |
EP3233033B1 EP3233033B1 (en) | 2020-06-17 |
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ID=54705570
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EP15801358.1A Active EP3233033B1 (en) | 2014-12-17 | 2015-11-17 | Resorcinol derivatives in compositions for simultaneous reshaping and colouring of keratinous fibres |
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Country | Link |
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US (1) | US10307354B2 (en) |
EP (1) | EP3233033B1 (en) |
DE (1) | DE102014226320A1 (en) |
WO (1) | WO2016096283A1 (en) |
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JP2019043886A (en) * | 2017-09-01 | 2019-03-22 | 日光ケミカルズ株式会社 | Discoloring inhibitor |
EP4076675A1 (en) * | 2019-12-20 | 2022-10-26 | L'Oréal | Multiple-compartment device comprising at least one internal frangible seal containing a keratin fibers dyeing composition |
ES2837489B2 (en) * | 2019-12-31 | 2022-02-28 | Primalchit Solutions S L | MIXTURE OF NON-POLYMERIC ORGANIC COMPONENTS WITH FLAME RETARDANT CAPACITY, METHOD OF PREPARATION AND USE |
Family Cites Families (11)
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US5196189A (en) * | 1974-05-16 | 1993-03-23 | Societe Anonyme Dite: L'oreal | Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin |
JPH0745385B2 (en) * | 1987-03-31 | 1995-05-17 | 協和醗酵工業株式会社 | Cosmetic composition for hair |
EP0352375B1 (en) | 1988-07-26 | 1994-11-02 | Teh-Shan Chang | Preparation for dyeing and setting hair |
DE19713698C1 (en) | 1997-04-03 | 1998-06-04 | Goldwell Gmbh | Dyeing and perming hair |
PL195678B1 (en) * | 1998-03-06 | 2007-10-31 | Oreal | Method of and cationic amphophilic polymer containing compositions for oxidisingly dyeing creatine fibre |
DE10143293A1 (en) | 2001-09-04 | 2003-03-20 | Wella Ag | Process for simultaneous coloring and permanent shaping of hair |
EP1743620A4 (en) * | 2004-04-27 | 2012-04-25 | Takasago Perfumery Co Ltd | Cosmetic hair prepartion composition |
DE102005061023A1 (en) | 2005-12-19 | 2007-06-21 | Henkel Kgaa | Process for the simultaneous dyeing and shaping of keratin-containing fibers |
DE102009054760A1 (en) * | 2009-12-16 | 2011-06-22 | Henkel AG & Co. KGaA, 40589 | 2-phase developer |
DE102010041035A1 (en) * | 2010-09-20 | 2012-03-22 | Henkel Ag & Co. Kgaa | Color retention by reducing agent-containing conditioning agents |
DE102011079643A1 (en) * | 2011-07-22 | 2013-01-24 | Henkel Ag & Co. Kgaa | New oxidation dye precursors |
-
2014
- 2014-12-17 DE DE102014226320.4A patent/DE102014226320A1/en not_active Withdrawn
-
2015
- 2015-11-17 EP EP15801358.1A patent/EP3233033B1/en active Active
- 2015-11-17 WO PCT/EP2015/076790 patent/WO2016096283A1/en active Application Filing
- 2015-11-17 US US15/539,232 patent/US10307354B2/en active Active
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WO2016096283A1 (en) | 2016-06-23 |
US10307354B2 (en) | 2019-06-04 |
US20180177697A1 (en) | 2018-06-28 |
EP3233033B1 (en) | 2020-06-17 |
DE102014226320A1 (en) | 2016-06-23 |
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